8-hydroxyheptadeca-4,6-diyn-3-yl ethanoate - Compound Card

8-hydroxyheptadeca-4,6-diyn-3-yl ethanoate

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8-hydroxyheptadeca-4,6-diyn-3-yl ethanoate

Structure
Zoomed Structure
  • Family: Plantae - Araliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Polyacetylene
Canonical Smiles CCCCCCCCCC(C#CC#CC(OC(=O)C)CC)O
InChI InChI=1S/C19H30O3/c1-4-6-7-8-9-10-11-14-18(21)15-12-13-16-19(5-2)22-17(3)20/h18-19,21H,4-11,14H2,1-3H3
InChIKey VAKXLUHTYNZAFY-UHFFFAOYSA-N
Formula C19H30O3
HBA 3
HBD 1
MW 306.45
Rotatable Bonds 10
TPSA 46.53
LogP 3.84
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 306.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cussonia zimmermannii Araliaceae Plantae 1899105

Showing of synonyms

  • Senn M, Gunzenhauser S, et al. (2007). Antiprotozoal polyacetylenes from the Tanzanian medicinal plant Cussonia zimmermannii. Journal of Natural Products,2007,70(10),1565-1569. [View] [PubMed]
Pubchem: 11522391
Nmrshiftdb2: 70126163

No compound-protein relationship available.

No scaffolds available.

Antiprotozoal

Absorption

Caco-2 (logPapp)
-4.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.01
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
20.86
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.49
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.02
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.99
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
6.34
Rat (Acute)
2.18
Rat (Chronic Oral)
1.82
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
339.08
Hydration Free Energy
-2.93
Log(D) at pH=7.4
4.11
Log(P)
5.77
Log S
-4.6
Log(Vapor Pressure)
-5.59
Melting Point
-7.86
pKa Acid
9.57
pKa Basic
1.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9227
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9227
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8775
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8775
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 3 0.8451
Peridinin-chlorophyll a protein, high-salt form O76183 O76183_AMPCA Amphidinium carterae 3 0.8451
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7832
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7832
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7810
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7810
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7697
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7697
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7691
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7691
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7600
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7600
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7594
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7594
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7567
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7567
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7541
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7541
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7517
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7517
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7516
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7516
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7482
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7482
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7447
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7447
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7446
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7446
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7445
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7445
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7398
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7398
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7394
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7394
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7389
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7389
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7354
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7354
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7350
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7350
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7335
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7335
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7331
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7331
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7309
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7309
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7293
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7293
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7287
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7287
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7282
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7282
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7275
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7275
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7273
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7273
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7260
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7260
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 2 0.7248
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 2 0.7248
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7247
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7247
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7233
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7233
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7230
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7230
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7228
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7228
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7202
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7202
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7199
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7199
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 2 0.7183
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 2 0.7183
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7162
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7162
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7157
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7157
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7147
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7147
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 2 0.7141
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 2 0.7141
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7129
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7129
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7123
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7123
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7106
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7106
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7100
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7100
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7096
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7096
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7088
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7088
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7012
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7012

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